Yarn conditioning process and compositions therefor



' Betept VJersey 1:15,'

invention relates to the conditiening o y"fof containing organic derivatives of cellulose textile yarn'sjlan'd nib `particularlyizcithecondkA suchasieelliilose'facetateg h lulo'se r'gniefderi-va ves,fitf is necessaryttret the llfarnfifn order: to`- reduce the te'rniency toward .breakage fof the individuali laments i' ornbers' wheri'f'lthey aresubjected t various mechalcl strains Fand 'i:oI-lb'ricate'"theyarriin'l order' 3Vtox r'fag' Y cilitte handlingiif-{sucli operations asfspinning, twisting: .vin'iidirrg 'an elirfijgLf-i i ift'X f isf'also' neces?. saryl t vre a`,t' y`arnftr'nca lptititor?use fas1w'arp. or llingorfor the manufacture of"variv: usl types of v liitted."fabrics; *In l'rnittingfv it isfparticularly 2Q.wherein B, is a substituent selected from the important thatY thej yanibesoft andplablein if groupwco'nsisting offxalkyl'pcyclalkyl, "aryl"y and order that itiay confor'mfreadily to thecontour heterocyclic -g'r '.\ups,: wherein Bland-R2 tare sub-' of 'the' needles and '.thusfzp'rodu'ce ar closely knit stituents selected fromfthe' group a"consisting'i of fabric freeV from .such defects as stitch distor'- hydrogen, alkyl,'cycloalkyLaryl-and"hetero'cyclic tion, pin holes, laddering-, and-the'llke." A25 groups and 'wherelnf R3:.is` a substituentv selectezl "Heretofore it has'beenwproposed to ernployzf` l1' from thegroup consisting? of hydrogen;alky1,`cy softening-agents such aspolyhydric alcohols and cloalkyl, aryl andl heterocyclic groupsv may be similar lagents asingredients of yarn condition-l used Tas yarn conditioning agents and .particularly ing or'lubricating formulas, lgenerallyin conjuncas softening agents, with or withoutthev addition tion with mineral, animal or'vegetable oils. It 30 of animal, mineral, or vegetable oils, inthe't'reathas been found, however, that most of the known ment ofyarns'composedof or containing. organic softening agents and the various formulas .conderivatives of cellulose.. We have lfound that taining them have certain drawbacks, one of the these compounds Whenv employed as describedin most serious of which is highvapor pressure, and the detailedvv examples setv forth fbelow have a in some cases too drastica solvent action on the 35 slight solvent and/or softening action on celluyarn. Many of such agents possess slight or lose organic derivative yarns which renders such insuilicient solvent power for thc lubricants with yarns soft and pliable without at 'the same time which they are used, and it isy accordingly nec. having too drastic an action thereon.v The alkyl essary to employ blending agents or emulsifying 'group may be selected from methyl, ethyl, agents in order to'obtain operable yarn treating 40 butyl, cyclo alkyLbenzyl, cetyl, ethoxyethyl, allyl formulas. In addition, many ofthe known sofand tetrahydrofurfuryl and the' like. The aryl tening and lubricating agents are insuiliciently group may be phenyl, Zenyl, naphthyl andffulyl. soluble in water to permit satisfactory removal etc. The heterocyclic group, for example, may by aqueous scour baths. n be tetrahydrofurfuryl, morpholine, etc.

This invention has as its principal object to 45 Typical compounds falling within the above provide a new class of yarn conditioning agents classification may be prepared as described -by particularly adapted for the conditioning of Tsuzuki, BuILChem. Soc. Japan, 12,1487 (1937).

yarns composed of or containing organic deriva- This process of kpreparation may be extended to tives of cellulose and capable of lubricating, softhev preparation lof' derivatives 'of the `above tening and rendering such yarns more amenable 50 compounds.-l w to knitting and other textile operations.. yA fur- In accordance'with the invention these comther and specic object is to provide a class pounds may beapplieddirectly. tofthe'yarnldurof conditioning agents which augment or assist `ing or after spinning; or` may be addedgto'the the lubricating action of various lubricants when ,g spinning'i `solutionitself..l We yhave found w'that applied'to 4such yarns. Astill further object is 55 these compounds have exceptional solventl to provide yarn softening and lubricating formu- 1 which i enable .thern `lto"dissolve minerale las'which can be readily removed from the yarns blown and unblown, dryi'ngfand semi-dryln by theisual scour baths. ,FA still further object etablefandanil'vrxal foils and accordingly t is toprovide an improved method for the' vcon-` Y be,`"and preferablyiar mp1eyedv 1 i' ditioning of yarnsV'particularly those composed 60 of yarn-conditioning or lubricatingformulas conjunction-.with agents which `function wholly or partially as lubricants.

In the following examples and description we have set forth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and notl as a limitation thereof, .I Our invention will be more readily understood by reference to the following examples in which typical applications of the invention are -set forth. y

Example 1 '(Diethyl tartrate cyclohexyl ketal)` is applied to textile materials (silk, wool, cotton,

e cellulose acetate, viscose, etc.) by means of a bath-wick, roller, spray, etc. to facilitate their knitting, weaving, spinning and the like. If vthe yarn is intended primarily for knitting, the amount 4of conditioning liquid applied may vary from 2 to 25 per cent by weight ofthe yarn. If the yarn is intended primarily for weaving, the amount of conditioning liquid applied may Vary between 1 and 5 per cent by weight of the yarn;

Example 2 E O E o-vC-o-o Er Naphthenyl-C O O-G O Et (Diethyl tartrate naphthenylal) the yarn.

provedresults in various textile operations such` as weaving, knittng,-etc.

Compositions particularly useful for the conditoning of various types of yarns in accordance with our invention particularly those composed of or containing cellulose acetate, cellulose ace- I tate propionate, cellulose acetate buty'rate, and

lsimilar organic acid esters, are as follows:

Example 3 A conditioning liquid is made up as follows:

Parts Olive oil 99-1 H H C-C-O oleyl HzC-C H2 o l H/ HIC\ /C-C\ 1-99 o H o\ c-o-o-,c H3 H (Oleyl methyl tartrate tetrahydrofural) This is applied to textile materials such as silk, wool, cellulose acetate, etc., as described in yIEIxample 1. If the yarn is intended primarily for knitting, the amount of conditioning' liquid applied may vary between 2 and 25 per cent by weight of the yarn, and if for weaving, the amount of liquid applied may vary between 1 and 5 per cent by weight of the yarn. Cellulose acetate illaments or bers treated as described above are quite soft and pliable and give im- Example 4 DE; E, (u) i (IJHzCH: O-C-C-O-C E12-CH CH: f Parts C 0 75-99 O-C-C-O-cetyl H ll CIHI O (Tetrahydrofuriuryl cetyl tartrate methylbutyl kctal) Beta-methoxyethyl succinate .Ll 25-1 Example 5 Naphthenyl O H. Il /O-CC-OC2HOCH3 C l 7S-99 O-C-C-OCzHi-O-CHa El Il 0 Naphthenyl (Di-beta-methoxy ethyl tartrate dinaphthenyl ketal) l: Tetrahydrofurlurylformal 25-1 Example 6 Il O-C-C-OCrHm H/ .A CgHr--C 1-30 O-I-C-C-OCiHl r H (Di-butyl tartrate butanal) Blown olive ol 99-70 Example 7 H CH3 O-C-C-O-cyclohexyl /C\` 1-40 CH: O--C-C-O-benzyl H l Il 0 (Cyclohexyl benzyl tartrate acetoneal) Neats-loot oil 99-60 Example 8 H Il /O C-C-O C2H4-OCzH5 B2C 1-50 0 C-C-O 01H4 (Di-beta-ethoxy ethyl tartrate formal) Blown neats-ioot oil 99-50 Example 9 O H Il /O-C-C-O naphthenyl CH3-0-CaH4-O CH2-CH\ l .u 1-99 O-C-C-O naphthenyl (Dinaphthenyl tartrate beta-mcthoxy-beta-ethoxy ethyl acetal) Sperm oil 99-1 2,249,519 l u l 3 Ose-0cm.

CH3 (Di-beta-methoxy ethyl tartrate methyl naphthenyl ketel) Mineral oil Ezamplelz Mineral oil o 30 naphthenyl H l O-C-C-O-CgHi--O CH; C 30 i O- -C-O-CzH4-OCH1\ CH: (Di-beta-methoxy ethyl tai-trate methyl naphthenyl ketel) Blown neats-foot oil OIyl nlnnhnl 5 Tetrahydrofurfuryl tetrahydroiuroate 5 Example 13 Mineral oil-.. 70-50 Oleic acid 1-25 n Il O-C-C-O naphthenyl CHa-O-CxHrO-CHz-CH 29-25 O-C-C-O naphthenyl H Il (Dinaphthenyl tartrate beta-methoxy-betaethoxy ethyl acetal) H l! /C-C-O naphthenyl O CHa-O-CzHl-Q-ClEh-CH 16-5 C-C-O naphthenyl H Il (Dinaphthenyl tartrate-beta-inethoxy-beta-ethoxy-ethyl aoetal) Sodium sulfate 2-0 Oleio acid 1-25 Ho iloNa y 110 (L, o oNa Example 16 Parts Beta-methoxyethyl adipate Blown neats-foot oil 30 Bullonated olive oil 10v Mineral oil 10 leic acid 10 N aphthenyl H 0-C-C-0-CzH4-O-CH| .I 10

O--C-C-O-CzH4-O-CH:

Naphthenyl (Di-beta-methoxy ethyl tartrate dinaphtlienyl ketel) Ethanolamine 8 Water.-- 'I Example 17 A 20 per cent solution of cellulose acetate in acetone in which is incorporated 1-25 'per cent by weight of the cellulose acetate of the com- 20 pound in Example 9 above is extruded through 7o ne oriilces into an evaporative atmosphere. The ilaments thus produced are wound, or twisted and'wound. Yarns produced from filaments thus prepared are pliable and suitable for 25 knitting'.

Any of the above compositions may be applied to the yarn intended for use in circular o knitting by means of a bath, wick, spray, roller,

pad or any suitable means. The amount offcon- 30 dition-liquid vapplied -may vary between 5-2 5% by weight of the yarn. Usually, however, the

amount of conditioning liquid applied 1is about 10-15% by weight of the yarn. Yarn composed of cellulose acetate conditioning as described above gives excellent results when used in the circular knitting process.

As will be apparent from the above examples and description the conditioning agents. of our invention may be applied by a wide variety of methods. For example, we may employ the agent as an ingredient of the spinning dope -from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulose derivative used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

If the conditioning agent is to lbe applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll, or felt wet therewith, or the liquid may be applied by immersion, spray, or otherwise. The particular point at which theliquid is applied may vary. It may, for example, beapplied to the yarn inside or outside the spinning cabinet,

between the guide andl godet roll, between the' godet or other roll or guide and' the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by the so-called "bobbin to bobbin" method. In the case of staple ber manufacture, the liqquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon .the results desired,-

the specific nature of the materialv to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in a given case where a. cellulose organic acid ester yarn such as a.- yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for Weaving, the amount may vary between about 1I and 5%.

Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other co1- oring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although we have found it" convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the specific action of the conditioning agent, the amount of the agent may be adjusted as, for example, by reducing the amount of the agent and corre-l spondingly increasing the amount of oil or other ingredient.

While we have described our invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of laments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial laments or a composite thread formed by twisting together individual strands of natural or artiiicial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the yarn material. Another outstanding characteristicof these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture-of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like. l

Of the above compositions we have4 found; that di-beta-ethoxy ethyl tartrate formal, cyl' clohexyl benzyl tartrate acetoneal and dibutyl tartrate butanal are outstanding in their ability to lubricate and soften yarns composed of orcontaining organic derivatives of cellulose and render them amenable 'to a wide variety of textile operations, particularly knitting.

What we claim is:

l. The process of conditioning yarn -to render it more amenable to textile operations including knitting, weaving, spinning and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a compound selected from the group consisting of the ketals and acetals of tartaric acid having the general formula:

R1 oCfi-CooR R2 ooH-COOR wherein R is a substituent selected from the group consisting of alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R1 and R2 are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and-heterocyclic groups and wherein R3 is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups.

2. The process of conditioning yarn composed of or containing organic derivatives of cellulose to render it more amenable to textile operations including knitting, Weaving, spinning and the like which comprises applying thereto a lubrieating and softening composition containing as its essential lubricating and softening component a compound selected from the group consisting of the ketals and acetals of tartaric alcid having the general formula:

wherein R is a substituent selected from the group consisting of alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R1 and R2 are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups and wherein R3 is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating. and softening composition containing as its essential lubricating and softening component a compound selected from the group consisting of the ketals and acetals of tartaric acid having the general formula:

OCH-COOR heterocyclic groups, wherein R1 and R2 are substituents selected f rom' the group consisting of vhydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups and wherein Rs is a substituent selected from the group consisting of hydrogen, allai,- cycloalkyl, aryl and heterocyclic groups.

4. 'Ihe process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like. which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component di-betaethoxy ethyl tartrate formal.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to vtextile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component cyclohexyl benzyl tartrate acetoneal.v

6. 'Ihe process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing asits essential lubricating and softening component dibutyl tartrate butanal.

GCH-GOORa the ketals and acetals of `tartaric acid havingl the general formula:

Oi'JliiI-COORI wherein R is a substituent selected from the group consisting oi'v alkyl, cycloalkyl, aryl and heterocyclic groups, wherein 1l.1 and R2 are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups and wherein R3 isy a substituent selected from the group consisting of hydrogen, alkyl,

cycloalkyl, aryl and heterocyclic groups.

9. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and. the

like, impregnated with a lubricant comprising.

di'betaethoxy ethyl tartrate formal.

10. Textile yarns composed ofvor containing cellulose acetate amenable to'textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising cyclohexylbenzyl tartrate acetoneal.

11. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising dibutyl tartrate butanal.

JOSEPH BQ Diem, .mms G. McNALLY. 

